Diethyl Ether → HCID 13557238, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 2.0 grams (0.02 mole) of O,N-dimethylhydroxylamine hydrochloride in 25 ml of dry tetrahydrofuran was cooled to -30° C. and 2.0 grams (0.02 mole) of triethylamine in 25 ml of dry tetrahydrofuran was added. The reaction mixture was stirred for 20 minutes and 5.6 grams (0.02 mole) of 2-(2-chloro-4-isocyanatophenyl)methyl-4,4-dimethyl-3-isoxazolidinone in 75 ml of dry tetrahydrofuran was added dropwise. The reaction mixture temperature was maintained at -30° C. throughout the addition. Upon completion of addition the reaction mixture was allowed to warm to ambient temperature as it stirred for 16 hours. The reaction mixture was heated under reflux for one hour then cooled to ambient temperature. The reaction mixture was placed in a separatory funnel and 20 ml of diethyl ether was added. The mixture was washed with three portions of 50 ml each of water, then dried with sodium sulfate. The mixture was filtered and the filtrate concentrated under reduced pressure to a residual oil. The oil was crystallized from heptane/ethyl acetate to give 4.2 grams of 2-(2-chloro-4-[(N-methoxy-N-methylamino)carbonylamino]phenyl)methyl-4,4-dimethyl-3-isoxazolidinone; m.p. 93°-95° C.

Provenance & Evidence